The present invention relates to a novel N-substituted-3-halopropiolamide compound, a method of producing the same compound, and a composition for controlling noxious organisms containing the same compound.
It has been reported by Yamazoe et al. that certain propiolic acid derivatives and propiolamide derivatives exhibit antifungal activity [Japanese J. Pharmacology, Vol. 102, page 278 (1982)]. N-(substituted phenyl)propiolamide is known to exhibit bactericidal activity, wood preservative activity, and repelling activity for water microbial [disclosed in Japanese Patent Publication Nos. 14756/1965, 31220/1969, and 58885/1985, respectively]. It is also reported that 3-iodopropiolic acid (I--C.tbd.C--COOH) and esters or derivatives thereof have exhibited antifungal activity [Ann. Applied Biol., Vol. 36, page 250 (1949); Japanese J. Pharmacology, Vol. 90, page 1578 (1970)]. The present patent assignee synthesized a large number of N-substituted-3-iodopropiolamides and reported that these compounds have antibacterial and antifungal activities [European Patent No. 0519427 (A1)].
On the other hand, 3-chloropropiolamide (Cl--C.tbd.CONH.sub.2), N-branched alkyl derivatives thereof and bridged ring alkyl-substituted derivatives thereof are known compounds, of which biological activities are not disclosed [J. Chem. Soc. C, (3), page 406 (1969); J. Chem. Soc. C, (11), page 2147 (1971); Japanese Patent Publication No. 17579/1978]. Further, 3-bromopropiolic acid (Br--C.tbd.COOH.sub.2) and methyl 3-bromopropiolate (Br--C.tbd.CO.sub.2 CH.sub.3) are known compounds, of which biological activities are not disclosed [Berichte, Vol. 63B, page 1868 (1930); J. Am. Chem. Soc., Vol. 71, page 2948 (1949); Ann. Chem., Vol. 2, page 819 (1957); Japanese Patent Publication No. 40402/1988; Synth. Comm., Vol. 22, page 567 (1992)].
Accordingly, an object of the present invention is to provide a novel compound which has a different chemical structure from those of the compounds disclosed in the above mentioned articles and patent gazettes, and which exhibits superior antibacterial and antifungal activities.